US7166722B2 - N-{2-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-n′-(5-methyl-3-isoxazolyl)urea salt in crystalline form - Google Patents

N-{2-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-n′-(5-methyl-3-isoxazolyl)urea salt in crystalline form Download PDF

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US7166722B2
US7166722B2 US10/532,104 US53210405A US7166722B2 US 7166722 B2 US7166722 B2 US 7166722B2 US 53210405 A US53210405 A US 53210405A US 7166722 B2 US7166722 B2 US 7166722B2
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crystal
dimethoxy
oxy
chloro
quinolyl
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US20060052415A1 (en
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Naoki Matsunaga
Satoshi Yoshida
Ayako Yoshino
Tatsuo Nakajima
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KH Neochem Co Ltd
Kyowa Kirin Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Definitions

  • pharmaceutically acceptable salt refers to a salt that is suitable for use as pharmaceutical preparations and is basically harmless to organisms.
  • Such pharmaceutically acceptable salts include those derived from pharmaceutically acceptable inorganic acids or organic acids, that is, inorganic acid salts or organic acid salts.
  • said process comprising the steps of: adding methanol to N- ⁇ 2-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl ⁇ -N′-(5-methyl-3-isoxazolyl)urea, adding a solution of maleic acid in methanol dropwise thereto, stirring the mixture to give a maleate of N- ⁇ 2-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl ⁇ -N′-(5-methyl-3-isoxazolyl)urea, and
  • form I to IV crystals of maleate can be produced by any of the methods described in Examples 16 to 19 which will be described later.
  • the pharmaceutical composition according to the present invention can be used for the therapy of a disease selected from the group consisting of tumors, diabetic retinopathy, chronic rheumatism, psoriasis, atherosclerosis, Kaposi's sarcoma, and exudation type age-related maculopathy. Further, the pharmaceutical composition according to the present invention can be used in the prophylaxis of metastasis or therapy of solid tumors.
  • the pharmaceutical composition according to the present invention is preferably administered orally.
  • 3,4-Dimethoxyacetophenone (1500 g) was dissolved in 170% nitric acid (1400 g) at 5 to 10° C. to prepare a solution which was then slowly added dropwise to a mixed solution composed of 67% nitric acid (8430 g) and sodium nitrite (18 g) at 5 to 10° C. over a period of 2 to 3 hr. After the completion of the dropwise addition, the reaction solution was stirred at 5 to 10° C. for 1 to 2 hr. Cold water (7.5 L) was added thereto, and the mixture was stirred for 30 min. The reaction solution was then filtered and was washed with water (30 L).
  • Phenyl chlorocarbonate (601 g) was added dropwise to 3-amino-5-methylisoxazole (377 g), pyridine (1215 g), and N,N-dimethylacetamide (4 L) at 0° C., and the mixture was stirred at 20° C. for 2 hr.
  • 4-[(4-Amino-3-chlorophenol)oxy]-6,7-dimethoxyquinoline (847 g) was added to the reaction solution, and the mixture was stirred at 80° C. for 5 hr.
  • the reaction solution was cooled to 5° C. Thereafter, methanol (8.5 L) and water (8.5 L) were added thereto, and the mixture was neutralized with an aqueous sodium hydroxide solution.
  • FIG. 9 shows a differential scanning calorimetrically measured chart for the crystal with an endothermic peak at a temperature around 120° C. and an exothermic peak at a temperature around 220° C.
  • FIG. 10 is a thermogravimetrically measured chart for the crystal.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Oncology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
US10/532,104 2002-10-21 2003-10-21 N-{2-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-n′-(5-methyl-3-isoxazolyl)urea salt in crystalline form Active 2028-11-16 US7166722B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2002306101 2002-10-21
JP2002-306101 2002-10-21
PCT/JP2003/013439 WO2004035572A1 (ja) 2002-10-21 2003-10-21 Ｎ−｛２−クロロ−４−［（６，７−ジメトキシ−４−キノリル）オキシ］フェニル｝−ｎ’−（５−メチル−３−イソキサゾリル）ウレアの塩の結晶形

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US7166722B2 true US7166722B2 (en) 2007-01-23

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US (1) US7166722B2 (de)
EP (1) EP1559715B1 (de)
JP (1) JP3763414B2 (de)
AT (1) ATE374199T1 (de)
AU (1) AU2003301430A1 (de)
DE (1) DE60316590T2 (de)
DK (1) DK1559715T3 (de)
ES (1) ES2294317T3 (de)
PT (1) PT1559715E (de)
WO (1) WO2004035572A1 (de)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070027318A1 (en) * 1999-01-22 2007-02-01 Kirin Beer Kabushiki Kaisha Quinoline derivatives and quinazoline derivatives
CN103459373A (zh) * 2011-02-10 2013-12-18 埃克塞里艾克西斯公司 制备喹啉化合物的方法和含有所述化合物的药物组合物
US11504365B2 (en) 2018-11-05 2022-11-22 Aveo Pharmaceuticals, Inc. Use of tivozanib to treat subjects with refractory cancer
WO2023096651A1 (en) 2021-11-26 2023-06-01 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Methods for treating bile duct cancers with tivozanib
WO2024095127A1 (en) 2022-10-31 2024-05-10 Pliva Hrvatska D.O.O. Solid state forms of tivozanib and process for preparation thereof
WO2025120654A1 (en) * 2023-12-05 2025-06-12 Natco Pharma Limited An improved process for the preparation of tivozanib hydrochloride hydrate

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US7576074B2 (en) 2002-07-15 2009-08-18 Rice Kenneth D Receptor-type kinase modulators and methods of use
EP2210607B1 (de) 2003-09-26 2011-08-17 Exelixis Inc. N-[3-fluoro-4-({6-(methyloxy)-7-[(3-morpholin-4-ylpropyl)oxy]quinolin-4-yl}oxy)phenyl]-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamid zur Behandlung von Krebs
EP1797037B1 (de) * 2004-09-29 2014-12-17 Bayer HealthCare LLC Verfahren zur herstellung von 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenyoxy}n-methylpyridin-2-carboxamid
TW200640443A (en) * 2005-02-23 2006-12-01 Alcon Inc Methods for treating ocular angiogenesis, retinal edema, retinal ischemia, and diabetic retinopathy using selective RTK inhibitors
US9037466B2 (en) * 2006-03-09 2015-05-19 Nuance Communications, Inc. Email administration for rendering email on a digital audio player
NZ779754A (en) 2009-01-16 2023-04-28 Exelixis Inc Malate salt of n-(4-{ [6,7-bis(methyloxy)quinolin-4-yl] oxy} phenyl)-n’-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide, and crystalline forms thereof for the treatment of cancer
UA108618C2 (uk) 2009-08-07 2015-05-25 Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку
US7998973B2 (en) * 2009-11-13 2011-08-16 Aveo Pharmaceuticals, Inc. Tivozanib and temsirolimus in combination
MX352926B (es) 2010-09-27 2017-12-14 Exelixis Inc Inhibidores dobles de met y factor de crecimiento endotelial vascular (vegf) para el tratamiento de cancer de prostata resistente a la castracion y metastasis osteoblasticas en los huesos.
CN102532116B (zh) * 2011-08-09 2015-01-21 武汉迈德森医药科技有限公司 抗肿瘤靶向治疗药物tivozanib的合成方法
CN104072492A (zh) * 2013-11-27 2014-10-01 苏州摩尔医药有限公司 一种抗肿瘤靶向治疗药物Tivozanib的合成方法
JP6328860B1 (ja) * 2016-09-13 2018-05-23 協和発酵キリン株式会社 医薬組成物
CN114213404B (zh) * 2021-12-27 2024-08-06 武汉九州钰民医药科技有限公司 Vegfr抑制剂替沃扎尼的合成工艺
US20260049059A1 (en) 2022-11-25 2026-02-19 Synthon B.V. A process for preparation of cabozantinib or tivozanib
CN117327061A (zh) * 2023-09-12 2024-01-02 武汉迈德森医药科技股份有限公司 一种替沃扎尼盐酸盐的制备方法及相关物质
CN117417336A (zh) * 2023-10-19 2024-01-19 武汉迈德森医药科技股份有限公司 一种替沃扎尼对甲苯磺酸盐的晶型及其制备方法和应用
WO2025220660A1 (ja) * 2024-04-15 2025-10-23 協和キリン株式会社 チボザニブ原薬およびその製造方法

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WO1999032106A1 (en) 1997-12-22 1999-07-01 Bayer Corporation Inhibition of raf kinase using substituted heterocyclic ureas
WO2001047890A1 (en) 1999-12-24 2001-07-05 Kirin Beer Kabushiki Kaisha Quinoline and quinazoline derivatives and drugs containing the same
WO2002032872A1 (fr) 2000-10-20 2002-04-25 Eisai Co., Ltd. Composes a noyau aromatique azote
WO2002088110A1 (en) 2001-04-27 2002-11-07 Kirin Beer Kabushiki Kaisha Quinoline derivative having azolyl group and quinazoline derivative
WO2004060373A1 (ja) * 2002-12-27 2004-07-22 Santen Pharmaceutical Co., Ltd. 滲出型加齢黄斑変性治療剤

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WO2001047890A1 (en) 1999-12-24 2001-07-05 Kirin Beer Kabushiki Kaisha Quinoline and quinazoline derivatives and drugs containing the same
US20040132727A1 (en) * 1999-12-24 2004-07-08 Teruyuki Sakai Quinoline and quinazoline derivatives and drugs containing the same
WO2002032872A1 (fr) 2000-10-20 2002-04-25 Eisai Co., Ltd. Composes a noyau aromatique azote
WO2002088110A1 (en) 2001-04-27 2002-11-07 Kirin Beer Kabushiki Kaisha Quinoline derivative having azolyl group and quinazoline derivative
US6821987B2 (en) * 2001-04-27 2004-11-23 Kirin Beer Kabushiki Kaisha Quinoline derivatives and quinazoline derivatives having azolyl group
WO2004060373A1 (ja) * 2002-12-27 2004-07-22 Santen Pharmaceutical Co., Ltd. 滲出型加齢黄斑変性治療剤

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070027318A1 (en) * 1999-01-22 2007-02-01 Kirin Beer Kabushiki Kaisha Quinoline derivatives and quinazoline derivatives
CN103459373A (zh) * 2011-02-10 2013-12-18 埃克塞里艾克西斯公司 制备喹啉化合物的方法和含有所述化合物的药物组合物
US9717720B2 (en) 2011-02-10 2017-08-01 Exelixis, Inc. Processes for preparing quinoline compounds and pharmaceutical compositions containing such compounds
CN103459373B (zh) * 2011-02-10 2018-02-23 埃克塞里艾克西斯公司 制备喹啉化合物的方法和含有所述化合物的药物组合物
US10123999B2 (en) 2011-02-10 2018-11-13 Exelixis, Inc. Processes for preparing quinoline compounds and pharmaceutical compositions containing such compounds
US10543206B2 (en) 2011-02-10 2020-01-28 Exelixis, Inc. Processes for preparing quinoline compounds and pharmaceutical compositions containing such compounds
US11298349B2 (en) 2011-02-10 2022-04-12 Exelixis, Inc. Processes for preparing quinoline compounds and pharmaceutical compositions containing such compounds
US12128039B2 (en) 2011-02-10 2024-10-29 Exelixis, Inc. Processes for preparing quinoline compounds and pharmaceutical compositions containing such compounds
US11504365B2 (en) 2018-11-05 2022-11-22 Aveo Pharmaceuticals, Inc. Use of tivozanib to treat subjects with refractory cancer
WO2023096651A1 (en) 2021-11-26 2023-06-01 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Methods for treating bile duct cancers with tivozanib
WO2024095127A1 (en) 2022-10-31 2024-05-10 Pliva Hrvatska D.O.O. Solid state forms of tivozanib and process for preparation thereof
WO2025120654A1 (en) * 2023-12-05 2025-06-12 Natco Pharma Limited An improved process for the preparation of tivozanib hydrochloride hydrate

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Publication number Publication date
DE60316590D1 (en) 2007-11-08
ES2294317T3 (es) 2008-04-01
JPWO2004035572A1 (ja) 2006-02-16
US20060052415A1 (en) 2006-03-09
EP1559715A1 (de) 2005-08-03
AU2003301430A1 (en) 2004-05-04
JP3763414B2 (ja) 2006-04-05
PT1559715E (pt) 2007-10-24
WO2004035572A1 (ja) 2004-04-29
EP1559715B1 (de) 2007-09-26
DK1559715T3 (da) 2007-12-27
DE60316590T2 (de) 2008-06-19
ATE374199T1 (de) 2007-10-15
EP1559715A4 (de) 2006-03-29

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